Advertise on podcast: Freedom Looks Like This – solo travel for women over 40 ready to choose themselves

Jenny Cioto has had clients come back from a vacation and tell her they didn't enjoy it at all, because the whole time they knew it was all on the credit card. Jenny is a money and life coach with a very full house, and she still usually takes a trip on her own at least once a year, with the money already sitting in an account labelled vacation. So what would change if you could pay for a solo trip before you go? In this episode: A week alone at a beach houseAn account labelled vacationTen pieces and a fridge full of lettuceSwimming with dolphins, with the money set asideFree spirits and Vatican ticketsOne town overThis episode is for you if: You want a solo trip, but the money still feels like a someday conversationYou're a woman over 40 who looks after everyone else and feels guilty spending on yourselfYou've come home from a trip and kept paying for it long after you unpackedYou don't have someone who can take over at home, and you want to know what a smaller version of solo travel could look likeResources mentioned: Jenny Cioto and Pursuing True NorthEpisode 42 with Jillian Johnsrud, on pricing a trip line by lineEpisode 43, on what "I can't afford it" really meansThe Solo Trip Fit FinderSupport the show Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and start moving. New episodes every Wednesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Email: [email protected] Join Skool: https://freedomlookslikethis.com/community

Someone says a trip is too expensive, and someone else hears "I don't have the money," when what she actually meant was "I would never spend that much on a holiday." I used to say I couldn't afford things by default, and it took me years, and a $500 star sapphire in India, to realise that I didn't know what I meant when I said it. So what do you mean when you say you can't afford a trip? In this episode: A star sapphire in IndiaSeveral sentences, same wordsMental accounting and the "too much" jarHow I actually decideSaying no to $25,000Japan, but not right nowThis episode is for you if: You've said "I can't afford it" about a trip without stopping to ask what you really meantYou're a woman over 40 who is careful with money and still feels guilty spending it on yourselfYou dream about solo travel, but the trip keeps landing in the "maybe someday" pileYou want to make money decisions that fit your own values, not someone else's rulesResources mentioned: Mark Butler on Changes Big and Small, episode 74: the conversation that changed how I think about "expensive"Mental accounting, Richard Thaler's research on how we sort money into mental jarsEpisode 42 with Jillian Johnsrud, on pricing a trip line by lineThe Solo Trip Fit FinderSupport the show Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and start moving. New episodes every Wednesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Email: [email protected] Join Skool: https://freedomlookslikethis.com/community

Most of us say "I can't afford it" about a trip before we've ever sat down and worked out what it would cost. What if the number you keep saying no to is one you've never actually looked at? Jillian Johnsrud, author of Retire Often, has taken more than a dozen mini retirements, and she explains why a month away rarely costs what we imagine. She gives us a surprisingly easy way to turn a someday trip into a real decision you can make. In this episode: Mini retirements, not holidaysChipotle or salsa dancing in MexicoThe $12,000 math mistakeA $20,000 week in ParisStarting with a one- or two-week trip This episode is for you if: You've said "I can't afford it" about a trip you've never actually pricedYou're a woman over 40 who wants to travel solo and money feels like the wall you keep hittingYou only have a week or two of leave and wonder whether any of this applies to youYou're curious how a mini retirement or sabbatical could fit around your work and your life Resources mentioned: Retire Often by Jillian Johnsrud: her book on planning a month or more away from work, available wherever books are soldJillian's website and newsletter: https://www.jillianjohnsrud.comJillian on Instagram: https://www.instagram.com/jillianjohnsrud/ Support the show Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and start moving. New episodes every Wednesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Email: [email protected] Join Skool: https://freedomlookslikethis.com/community

Even when the place is beautiful and you are grateful to be there, a trip can still leave you depleted. I used to think that meant I had chosen wrong.  What I have come to think is that it is a question of fit, between what a place asks you to carry and what you were already carrying when you arrived. This one is from the vault, and it starts with a very long day in Kandy. In this episode: The twelve-hour tourTwo measurement systemsRain on the museum roofWhat you're already carryingThis episode is for you if: You came home from a good trip more tired than when you left, and you have never quite worked out whyYou're a solo female traveler who keeps adding one more stop because somebody said you shouldYou're a woman over 40 fitting travel around work, and the weekends are not restoring youYou have let somebody else decide what counts as worth seeingTake my fit finder quiz here: https://freedomlookslikethis.com/solo-trip-personality-quiz/ Support the show Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and start moving. New episodes every Wednesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Email: [email protected] Join Skool: https://freedomlookslikethis.com/community

I was on a walkway in Brazil, soaked through, my raincoat sitting on the bus, walking back as fast as I could and repeating under my breath, "This is crazy." Most weeks I talk about solo travel as practice for self-trust. But that Saturday at Iguazu Falls wasn't about practicing anything. And it made me wonder why so many of us need a reason before we let ourselves have the thing we love. In this episode: An update from the roadThe coati and the alfajorTwo sisters from belowA raincoat on the busThree frontiersLove is a reasonThis episode is for you if: you only let yourself go when you're burnt out enough to have earned ityou're a woman over 40 who keeps putting the thing you love behind everybody else's needsyou travel solo, or with friends, and are intrigued when you hear "pure delight"you've ever felt you had to justify a trip before it felt allowed Resources mentioned: Iguazu Falls blog post with photosLive Lab founding cohort available for $147.47, closes September 28 at 12:00 UTC. Email [email protected]. Support the show Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and start moving. New episodes every Wednesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Email: [email protected] Join Skool: https://freedomlookslikethis.com/community

By the time I actually landed in Lagos, everyone else had already been there for a full day because my visa came through late. Once I was there, surrounded by family for my stepmother's 61st birthday, the same skills solo travel built in me were still firing, in taking Uber to the grocery store, in figuring out a food delivery app alone in my room. How could this trip be mine as much as it was ours? I think the answer is yes. In this episode: The delayed landing in LagosTraveling with familyThe Uber grocery runSelf-efficacy, definedMine as much as oursThis episode is for you if: You've wondered if solo travel confidence holds up once you're surrounded by family againYou're planning a family or group trip and are worried you'll lose the version of yourself solo travel builtYou're a woman over 40 who notices old family patterns showing up the moment you're back in familiar situationsYou've ever reached for the easier, hands-off version of something instead of figuring it out yourself and wondered what that choice actually costs youResources mentioned: Episode 36 with Kristine Madera about belonging as a set of skills you build Support the show Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and start moving. New episodes every Wednesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Email: [email protected] Join Skool: https://freedomlookslikethis.com/community

I was standing in the corner of Edinburgh airport with two suitcases, a backpack, a side bag, and no visa, making call after call that went nowhere. The plan had been for my whole family to fly to Lagos together for my stepmother's 61st birthday. I had to let go of that plan at eight in the morning and what actually got me through the experience wasn't the thing I expected. In this episode: Checking the visa portal all night Alone at the Edinburgh check-inThe woman without the visaTrying to switch to Ghana insteadBuying two new ticketsSix hours in the airport loungeLanding in Lagos This episode is for you if: You've had travel plans nearly fall apart the night before you were supposed to leaveYou're a woman over 40 traveling with family and still figuring out how much of the decision-making is yoursYou've assumed a plan would hold and didn't check it until it was almost too lateYou're a solo female traveler who wants to hear what actually gets you through a travel disaster, not the highlight reelSupport the show Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and start moving. New episodes every Wednesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Email: [email protected] Join Skool: https://freedomlookslikethis.com/community

I'm bringing this one back from the vault. I recorded it in April, before this month took me through Nigeria, Ghana, and Rwanda, and before I missed an episode for the first time because I didn't have reliable internet. It still holds up. The next two episodes are going to get specific about this trip, the Nigerian visa that almost didn't come through in time, and what I learned about connecting with strangers. I left a fourteen-year teaching career without knowing what would come next. I remember standing on a balcony in Canada that September, watching a school bus go by, and feeling relief instead of grief. That relief was the confirmation, not a plan. Since then I've spent three months living as a digital nomad in Southeast Asia and built a life I would not have believed was available to me back then. None of it started with feeling ready. It started with one decision I was willing to name. In this episode: - The planning meeting that broke something - Watching the school bus go by - The conditions that kept multiplying - Clarity comes in the decision - Three months as a digital nomad - Naming the trip as a decision This episode is for you if: you keep waiting for one more condition to be met before you'll book the tripyou're a woman over 40 who left something certain for something you couldn't yet imagineyou think clarity has to arrive before the decision instead of inside ityou've been telling people about a trip for longer than six months and still haven't named a dateyou've caught yourself treating "someday" as a real plan instead of a way of avoiding one Resources mentioned: Laurie Santos's course The Science of WellbeintBarbara Oakley's Learning How to Learn Support the show Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and start moving. New episodes every Wednesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Email: [email protected] Join Skool: https://freedomlookslikethis.com/community

You never find somebody who's just like you, not even twins. My guest today, Kristine Madera, has backpacked solo through China, Russia, and the Baltics during the fall of the Soviet Union, served in the Peace Corps in Papua New Guinea, taught English in Japan, and spent years since teaching other travelers how to belong in cultures that were never built around them. We get into the two-minute trick a Peace Corps trainer taught women stationed in Papua New Guinea, why small talk is never actually small when you're the one traveling alone, what to do when someone comes on too strong in a culture that isn't yours, and what it means to belong In this episode:  The Dali hostel, sixteen strangers, one hourBelonging to yourselfThe Papua New Guinea micro-tribe trickSmall talk as the doorPacing yourself as an introvertsPracticing curiosity as a skillThis episode is for you if:  you've walked into a room full of strangers and felt like everyone else already knew each otheryou're a solo female traveler who wants real connection, not just polite distanceyou're an introvert, or a recovering shy introvert, who assumes small talk isn't for youyou're a woman over 40 who's curious about other cultures but isn't sure where you actually belong in themyou've ever needed permission to say "I just need a few minutes"For more from Kristine, see The Art of Belonging (free guide) Support the show Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and start moving. New episodes every Wednesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Email: [email protected] Join Skool: https://freedomlookslikethis.com/community

I recorded this one a while back, and in it I explore a feeling so many of us have after 40, where you walk into a room and somehow nobody quite registers that you're there. Back then I thought the answer was to be seen again, to be noticed, and that if I could just be visible then the rest would sort itself out. I'd say it a bit differently now. I've pulled the episode from the vault because the question underneath it still holds up. I talk about the small everyday versions of this and why travel makes all  so hard to ignore. Here's what I've come to think since. Invisibility isn't really the deepest problem.  While I've left the original episode the way it was,  at the end I come back and add the part I didn't have words for yet, plus a small invitation you can actually try this week. In this episode: Airports and overhead binsThe chocolate shop in OmanWhen waiting becomes a habitFight, flight, freeze, fawnThe cost of walking awayChosen vs. imposed invisibilityBecoming visible to yourself firstWhat I'd add nowThis episode is for you if: you've stood clearly next in line and watched someone who arrived after you get helped firstyou travel solo, or you're thinking about it, and you've felt strangely easy to overlook when there's no one beside youyou're a woman over 40 who's tired of having to remind the world that you're right hereyou've felt that heat rise up in you when you're passed over, and you don't want to have to beg to be seenyou've wondered whether letting it go keeps the peace, or slowly trains you to abandon yourselfResources mentioned: Take the solo travel quiz at https://freedomlookslikethis.com/solo-trip-fit/ Support the show Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and start moving. New episodes every Wednesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Email: [email protected] Join Skool: https://freedomlookslikethis.com/community

A lot of us have a list somewhere, in a notes app or just in the back of our heads, of places we'd like to visit. Every place on it sounds lovely, and not one of them is an obvious yes. So we keep researching, and we keep not choosing. What if the way you've been choosing where to go is the very thing keeping you home? The best destination for you probably isn't the one the lists keep pushing, and it isn't the safest or the most impressive one either. There's a different question to ask first, and most of us have never been taught to ask it. This episode gets into why researching more makes the choice harder instead of easier, the reason a place that looks perfect online can leave you feeling almost nothing once you're standing in it, and four feelings I've chosen trips around, along with the very different places that gave them to me. The places are mine. The question underneath them might change how you pick your next one. In this episode: The 15 best places trapSituation selection, explainedFour feelingsYour invitationThis episode is for you if: you've saved a dozen versions of "the 10 best places for solo women over 40" and still can't commit to oneyou travel solo, or want to, and every option feels reasonable but none of them feels like yoursyou're a woman over 40 who has gotten so good at the sensible choice that the muscle for choosing what you actually want has gone quietyou once did the bucket-list trip and felt almost nothing, and you've never quite known whyResources mentioned: Take the solo trip personality quiz at freedomlookslikethis.com/solo-trip-fit/. Support the show Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and start moving. New episodes every Wednesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Email: [email protected] Join Skool: https://freedomlookslikethis.com/community

Safety can become a giant question, one that seems to require a single answer before we are allowed to book the trip. But that is not how it works when you are actually travelling. What matters is the judgment you build in the small moments: where you stay, how a street feels after dark, whether someone takes your question seriously, and what you need in order to settle into a place. This is an episode from the vault, and I am bringing it back because it is still one of the conversations we need to have before a solo trip. Solo travel safety for women is about learning how to pay attention without handing over your judgment or letting fear make every decision for you. I talk about arriving in Morocco after dark, learning how differently a place can feel as the light changes in the Indian Himalayas, and living in Sudan during the Darfur war. Those stories are not a way to make one rule for every place but there is a lesson that has stayed with me. I also talk about what it means to support your nervous system when you travel. I share some examples that have worked for me, to expose you to the possibilities and invite you to find out what works for you. You do not have to prove anything by travelling in a way that leaves you on edge. The point is to prepare well enough that you can be present once you get there. In this episode: The crossbody bag and the trip planWhat changes at duskReading a place beyond alertsThe danger of a single storyWhat supports your nervous systemStaying in relationship with safetyThis episode is for you if: you want to travel alone but safety is the question that stops every planyou are a woman over 40 who wants to prepare well without becoming consumed by worryyou have read so much advice about solo travel that you feel less clear than when you startedyou want to trust your own judgment in unfamiliar placesFor this weeks challenge, download the invitation at https://freedomlookslikethis.com/goalone. Support the show Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and start moving. New episodes every Wednesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Email: [email protected] Join Skool: https://freedomlookslikethis.com/community

People often ask me if I get lonely when I travel on my own, and it's a fair question. But after more than 40 solo trips, I realize that being alone and being lonely don't really have much to do with each other. I took myself to see The Devil Wears Prada, the musical, in London, on my own, with two empty seats beside me and a very tall woman right in front of me. What happened in that theater, along with a note from a subscriber, Irene, were important reminders for me. In this episode, I take apart the difference between loneliness and solitude. You can feel lonely in a marriage, in a crowd, or in the same loop of the same week and still feel completely content at a table for one. I get into the research on the capacity to be alone and share the small, ordinary shift that made solo travel feel lighter after 40. If you are a solo female traveler, or a woman who wants to be, and you keep bumping into the worry of what if I get lonely out there, this is the conversation for you. In this episode: The empty seats beside meTaking up space on your ownTaking a book to dinnerAlone vs lonelyOnwardThis episode is for you if: you've talked yourself out of a dinner, a show, or a trip because you'd have had to go on your ownyou travel solo, or want to, but the thought of a table for one in a bright room stops you coldyou're a woman over 40 who does alone at home easily, yet dreads being alone where other people can see youyou've reached for a book or your phone as a buffer so you don't look like the woman nobody came withTake the Solo Travel Fit Quiz at https://freedomlookslikethis.com/solo-trip-fit About Freedom Looks Like This Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and start moving. New episodes every Tuesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Support the show Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and start moving. New episodes every Wednesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Email: [email protected] Join Skool: https://freedomlookslikethis.com/community

We plan our trips around the famous sights, the must-do list, the things we'd feel a little silly skipping. And then we come home exhausted, having seen everything without focusing on enjoyment. What if the trip you'll actually enjoy is the one you subtract down to yourself? Think about the best afternoon you've ever had on a trip. I'd bet it wasn't the landmark everyone photographs. It might even be something you'd never have written on an itinerary, and you still think about it months later with a smile. This episode is about how to plan a solo trip around the woman who is actually going, not the one you think you should be, and it doesn't start with where to go but with a better question that prioritizes your enjoyment. We focus on a trip built for delight instead of for more, more, more, and the simple reason a choice that genuinely fits you, what psychologists call self-concordant, is the one you put more into and get more back out of. In this episode: - The afternoon that wasn't on the list - The myth of the one right trip - The subtraction effect - Being good company for yourself - The Krakow evening I skipped the sights - One swap before you go This episode is for you if: You've decided you want to travel solo and the planning advice you keep finding feels like it's written for somebody elseYou're worried you'll do everything right, see all the right sights, and still come home feeling like you didn't really enjoy itYou keep a famous landmark on the itinerary just because you'd feel silly skipping it, even though you don't actually want to goYou're a woman over 40 who wants a trip that fits the woman you are now, not a twenty-two-year-old backpacker with no preferencesYou already travel solo, or you want to, and you're ready for the how About Freedom Looks Like This: Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and give yourself permission to start moving. New episodes every Tuesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Support the show Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and start moving. New episodes every Wednesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Email: [email protected] Join Skool: https://freedomlookslikethis.com/community

We keep telling ourselves we'll take the trip we actually want once we've finally figured everything out. What if you have that backwards? You will not think your way to your next chapter from inside the old one, and the clarity you keep waiting for tends to arrive out in the doing, on the trip itself. This is the adult gap year, reimagined, and it does not have to be a year, or a leap, or anything as big as you are picturing. After all, this is not Eat, Pray, Love. In this episode: The season you didn't chooseThe trap of thinking harderThe habit discontinuity effectA quiet month in FlorenceInterrupting one autopilotThis episode is for you if: you're in a season that ended before you were ready, a role, a relationship, the shape of your household, and you keep waiting for clarity before you do anything about ityou've wanted a solo trip but told yourself you can't take the time, the job needs you, or you have to figure your whole life out firstyou've been calling this stretch a transition, or limbo, and some part of you is ready to do something with it instead of waiting it outyou're a woman over 40 in a midlife transition who wants to feel like yourself again, not just keep showing up for everyone elseyou already travel solo, or you want to, and you're ready for the how, and you've heard enough of the why About Freedom Looks Like This: Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and start moving. New episodes every Tuesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Support the show Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and start moving. New episodes every Wednesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics. Email: [email protected] Join Skool: https://freedomlookslikethis.com/community